Coloring material and color filter

ABSTRACT

There are provided a pigment-containing coloring material stably dispersible in a high concentration in various organic solvents, and a process for producing the same. The production process of the coloring material is characterized by comprising the steps of: providing a solution comprising (1) a soluble pigment precursor which is convertible into an insoluble pigment, (2) a solvent capable of dissolving the soluble pigment precursor therein, and (3) a stabilizing agent comprising an organic compound having a structure or a functional group capable of stabilizing the dispersibility of the insolubilized pigment in the solvent; and converting said soluble pigment precursor into an insoluble pigment to obtain the coloring material containing the insolubilized pigment dispersed stably in the solvent.

TECHNICAL FIELD

[0001] The present invention relates to a pigment-containing coloringmaterial stably dispersible in high concentration in various organicsolvents, and a process for producing the same.

[0002] This coloring material, as with conventional dyes or pigments, isused, either solely or after addition of an inverter component, asvarious coating systems, coating materials, printing inks, ink jetprinting inks, toners, or compositions. In particular, color filtersproduced from the coloring material according to the present inventioncan have improved spectral characteristics (higher color purity, highertransmittance, and higher contrast) than conventional color filters.

[0003] Thus, the present invention relates to a color filter possessingexcellent spectral characteristics (higher color purity, highertransmittance, and higher contrast) comprising a colored layercontaining a pigment stably dispersible in high concentration in variousorganic solvents, particularly to a color filter for use in color liquidcrystal displays.

BACKGROUND OF THE INVENTION

[0004] In general, dyes have unsatisfactory resistance to light, heat,solvents, and chemicals. On the other hand, pigments involve problems ofa lack of dispersion, dispersion stability, transparency, profilesharpness of absorption spectra or transmission spectra, or diffusion.In this respect, Japanese Patent Laid-Open No. 188234/1995 or JapanesePatent Laid-Open No. 6242/1996 proposes a novel coloring material havingboth an advantage of dyes and an advantage of pigments (good solubilityof dyes and good weathering resistance of pigments) through the use of asoluble pigment precursor which can be converted to insoluble pigmentparticles having a size of nanometers by a chemical, thermal, orphotolytic method or by laser or other beam irradiation.

[0005] The use of a coloring material disclosed in Japanese PatentLaid-Open No. 188234/1995 or Japanese Patent Laid-Open No. 6242/1996permits the pigment to be evenly dispersed in high concentration in apolymer layer, but on the other hand, there is a disadvantage thatelimination partially occurs due to volatilization of the precursor uponconversion of the soluble pigment precursor in the polymer layer toinsoluble pigment particles by chemical, thermal, photolytic, orradiation induced means, leading to an uneven reduction in layerthickness. In the case of the soluble pigment precursor, in general, abulky functional group is introduced to render the precursor soluble ina solvent, and the elimination of the bulky functional group convertsthe precursor to an insoluble pigment. This renders the aboveunfavorable tendency significant. Further, when the eliminatedfunctionality is present in a large amount in the layer, there is a fearof the influence of the functionality. For these reasons, it isdifficult to apply the coloring material to the field of applicationswhere dimensional accuracy, particularly good coating smoothness arerequired, such as color filters.

[0006] When the soluble pigment is converted to the insoluble pigment ina solvent before coating formation from the viewpoint of avoiding thisproblem, the precipitation of the pigment extremely lowers thesolubility of the pigment in the solvent, leading to the production ofcoagulation sediment. Therefore, the storage stability is poor, and thepreparation of a highly concentrated solution per se becomes difficult.

[0007] Meanwhile, in the case of liquid crystal displays, a liquidcrystal material is sealed into a gap of about 1 to 10 μm between glassor other transparent substrates provided with transparent electrodes,and the liquid crystal is aligned in a given direction by a voltageapplied across the electrodes to form transparent portions and opaqueportions, thereby displaying an image. For color liquid crystaldisplays, a color filter for three primary colors of light is providedon any one of the transparent electrode substrates, and the threeprimary colors are added by shutter operation of the liquid crystal todisplay desired colors.

[0008] The color filter used in the color liquid crystal displaycomprises a transparent substrate, a colored layer, a protective layer,and a transparent conductive layer stacked in that order. The colorfilter and electrodes or transparent electrodes provided with a thinfilm transistor, which face colored pixels of three primary colors ofRGB, are held while leaving a gap of several μm therebetween, and aliquid crystal material is sealed into between the gap to form a liquidcrystal display.

[0009] The colored pixels provided in the color filter are generallyformed of a specific colorant, such as a dye or a pigment, incombination with a suitable resin, a binder, a polymer and/or anadditive. Dyes generally have unsatisfactory resistance to light, heat,solvents, and chemicals. On the other hand, pigments involve problems ofa lack of dispersion, dispersion stability, transparency, profilesharpness of absorption spectra or transmission spectra, or diffusion.In this respect, Japanese Patent Laid-Open No. 188234/1995 or JapanesePatent Laid-Open No. 6242/1996 proposes a coloring material having bothan advantage of dyes and an advantage of pigments (good solubility ofdyes and good weathering resistance of pigments) through the use of asoluble pigment precursor which can be converted to insoluble pigmentparticles having a size of nanometers by chemical, thermal, orphotolytic means or by laser or other beam irradiation.

[0010] The use of a coloring material disclosed in Japanese PatentLaid-Open No. 188234/1995 or Japanese Patent Laid-Open No. 6242/1996permits the pigment to be evenly dispersed in high concentration in apolymer layer of the colored layer constituting the color filter, but onthe other hand, there is a disadvantage that elimination partiallyoccurs due to volatilization of the precursor upon conversion of thesoluble pigment precursor in the polymer layer to insoluble pigmentparticles by chemical, thermal, photolytic, or radiation induced means,leading to an uneven reduction in layer thickness. In the case of thesoluble pigment precursor, in general, a bulky functional group isintroduced to render the precursor soluble in a solvent, and theelimination of the bulky functional group converts the precursor to aninsoluble pigment. This renders the above unfavorable tendencysignificant. Further, when the eliminated functionality is present in alarge amount in the layer, there is a fear of the influence of thefunctionality. For these reasons, it is difficult to apply the coloringmaterial to the field of applications where dimensional accuracy,particularly good coating smoothness are required, such as colorfilters.

[0011] When the soluble pigment is converted to the insoluble pigment ina solvent before coating formation from the viewpoint of avoiding thisproblem, the precipitation of the pigment extremely lowers thesolubility of the pigment in the solvent, leading to the production ofcoagulation sediment. Therefore, the storage stability is poor, and thepreparation of a highly concentrated solution per se becomes difficult.

SUMMARY OF THE INVENTION

[0012] First Invention

[0013] The first invention has been made under these circumstances, andcan overcome the above problems, although the reason why the aboveproblems can be solved has not been fully elucidated. Specifically,according to the first invention, there are provided a coloring materialcomprising an insolubilized pigment dispersed stably in a solvent, saidcoloring material being produced by, in dissolving (1) a soluble pigmentprecursor, which is convertible into an insoluble pigment, in (2) asolvent capable of dissolving the soluble pigment precursor therein,allowing (3) a stabilizing agent, comprising an organic compound havinga structure or a functional group capable of stabilizing thedispersibility of the insolubilized pigment in the solvent, to furtherexist, and, in this system, converting said soluble pigment precursorinto an insoluble pigment, and a process for producing the same. Thefirst invention further includes a coloring material wherein the abovecoloring material has been concentrated to obtain a solidified coloringmaterial, and a process for producing the same. The first inventionfurther includes a coloring material wherein the above solidifiedcoloring material has been redispsersed in a solvent, and a process forproducing the same. The first invention further includes a coloringmaterial comprising an adduct formed by interaction between a solublepigment precursor convertible to the insoluble pigment and a stabilizingagent comprising an organic compound having a structure or a functionalgroup capable of stabilizing the dispersibility of the insolubilizedpigment in the solvent. In particular, the coloring material accordingto the present invention can solve the above problems, and can be usedin high concentration to easily form a pigment-dispersed polymer layerhaving excellent coating smoothness. This makes it possible to apply thecoloring material to color filters having improved spectralcharacteristics (higher color purity, higher transmittance, and highercontrast) as compared with color filters using conventional coloringmaterials.

[0014] Second Invention

[0015] According to the second invention, there is provided a colorfilter using a coloring material comprising an insolubilized pigmentdispersed stably in a solvent, said coloring material being produced by,in dissolving (1) a soluble pigment precursor, which is convertible intoan insoluble pigment, in (2) a solvent capable of dissolving the solublepigment precursor therein, allowing (3) a stabilizing agent, comprisingan organic compound having a structure or a functional group capable ofstabilizing dispersibility of the insolubilized pigment in the solvent,to further exist, and, in this system, converting said soluble pigmentprecursor into an insoluble pigment.

[0016] The coloring material may be in the form of a solidified coloringmaterial produced by concentrating the above coloring material, or maybe in the form of a dispersion produced by redispersing the resultantsolidified coloring material in a solvent. The second invention furtherincludes a technique wherein the coloring material is an adduct formedby interaction between a soluble pigment precursor convertible to theinsoluble pigment and a stabilizing agent comprising an organic compoundhaving a structure or a functional group capable of stabilizingdispersibility of the insolubilized pigment in the solvent. Inparticular, the coloring material according to the present invention cansolve the above problems, and can be used in high concentration toeasily form a pigment-dispersed polymer layer having excellent coatingsmoothness. This makes it possible to produce color filters havingimproved spectral characteristics (higher color purity, highertransmittance, and higher contrast) as compared with conventional colorfilters.

[0017] Third Invention

[0018] The third invention includes a color filter comprising a coloredlayer as colored pixels provided on a transparent substrate, the coloredlayer containing a specific pyrrolo[3,4-c]pyrrole derivative.

[0019] In the color filter according to this aspect of the presentinvention, a specific pyrrolo[3,4-c]pyrrole compound described later iscontained as a pigment in at least one colored pixel. The particlediameter of the pigment is not more than the wavelength of incidentlight, that is, in the range of 1 nm to 300 nm in terms of averageparticle diameter, and, at the same time, the particle diameterdistribution of the pigment falls within a specific range, that is, iswithin ±30% of the average particle diameter. By virtue of this, alowering in transmittance caused by light scattering can be suppressed,and, in its turn, a much improvement in transparency of the formedcolored pixels can be attained over the transparency of colored pixelsobtained using conventional pigment-dispersed systems.

[0020] Further, the pigment produced from the coloring material hasexcellent display quality, and thus can easily form colored pixels whichhave ideal spectral characteristics as a color filter, specifically havea spectral characteristic curve in a visible region such that the lighttransmittance in a light absorption region is in the range of 0 to 20%while the light transmittance in a light transmission region is not lessthan 50%.

[0021] The amount of the pigment produced from the coloring material canbe regulated by regulating the solid content of the matrix, specificallycan be regulated in the range of 10 to 90% by weight, and can be easilyused in higher concentration. Therefore, the contrast can also besignificantly improved over the contrast attained in the conventionalpigment-dispersed system, and can be set, for example, at not less than2,000.

[0022] In general, dyes have unsatisfactory resistance to light, heat,solvents, and chemicals. On the other hand, pigments involve problems ofa lack of dispersion, dispersion stability, transparency, profilesharpness of absorption spectra or transmission spectra, or diffusion.In this respect, Japanese Patent Laid-Open No. 188234/1995 proposes apigment precursor which has a carbamate group and can be converted intoa corresponding diketopyrrolopyrrole pigment having a size of nanometersby chemical, thermal, or photolytic means or by laser or other beamirradiation.

[0023] When the coloring material disclosed in Japanese Patent Laid-OpenNo. 188234/1995 is used, the affinity of the pigment precursorparticularly for aprotic solvents is imparted by suitably selectingsubstituents D and E in formula (I). In this case, in order to broadenthe range of selection of the solvent and, at the same time, to stablyand homogeneously disperse the pigment in high concentration, thesubstituent should be made bulky to such an extent that the half or moreof the molecular weight of the whole chemical compound is accounted forby this substituent. The introduction of the bulky substituent into thepigment, however, is very difficult. Further, these introducedsubstituents are finally eliminated by a chemical, thermal, photolytic,or radiation induced method. Therefore, finally increasing the pigmentconcentration becomes very difficult.

[0024] These adverse effects are particularly significant when thepigment precursor is converted to a pigment in a polymer layer. Thismakes it difficult to apply the pigment to the field of applicationswhere good dimensional accuracy, particularly good coating smoothness,is required, such as color filters.

[0025] The present invention has been made under these circumstances,and can overcome the above problems, although the principle on which theproblems can be overcome has not been fully elucidated. Specifically,according to the present invention, chemically cleaving a bond between Nand C═O in at least one pyrrolo[3,4-c]pyrroleketopyrrole group offormula (I) can enhance the affinity of the compound per se for varioussolvents, and thus enables a pigment-dispersed polymer layer having ahigh pigment content and excellent coating smoothness to be easilyformed. This can realize a color filter having significantly improvedspectral characteristics (higher color purity, higher transmittance, andhigher contrast) over the conventional color filters.

BRIEF DESCRIPTION OF THE DRAWINGS

[0026]FIG. 1 is a ¹H-NMR spectrum chart of a solidified coloringmaterial produced in an example of the present invention; and

[0027] FIGS. 2 to 5 are ¹H-NMR spectrum charts of coloring materialsproduced in examples of the present invention.

BEST MODE FOR CARRYING OUT THE INVENTION

[0028] First Invention

[0029] The present invention is attained by dissolving, in a solvent tosaturation, an organic compound having a structure or a functional groupcapable of stabilizing the dispersibility of an insolubilized pigment inthe solvent and a soluble pigment precursor convertible into aninsoluble pigment and applying chemical means, thermal means, photolyticmeans, radiation induced means, or means comprising a combination of twoor more of the above means to convert at least a part of the precursorto a pigment. By virtue of the presence of the organic compound having astructure or a functional group capable of stabilizing thedispersibility of an insolubilized pigment in the solvent, the coloringmaterial, even when concentrated after the conversion of the solubleprecursor to the pigment, is free from any precipitate and anysignificant floating matter. Therefore, a highly concentrated dispersionof the soluble precursor, at least a part of which has been converted toa pigment, can be easily realized. This can overcome the above problemscaused by conversion to an insoluble pigment, for example, after coatingformation.

[0030] The coloring material according to the present invention, evenwhen concentrated, can be stably present. When the coloring material isfurther concentrated, the coloring material is precipitated as solidmatter. This solid matter is sometimes crystalline, can be easilyisolated from the dispersion, and as such can be stably stored for along period of time. The isolation of the solid matter from thedispersion permits impurities, such as excess stabilizing agent, to beeasily removed, for example, by washing.

[0031] Further, the solidified coloring material according to thepresent invention, together with a solvent in which an insoluble pigmentper se cannot be easily dispersed, can easily constitute a stabledispersion or a highly concentrated solution thereof without providingany complicate step of dispersion or use of any dispersant for apigment.

[0032] Although the reason for this has not been fully elucidated, thereason is believed to reside in that, in the course of conversion of thesoluble pigment precursor into the insoluble pigment, interaction on amolecular level between the stabilizing agent and the insoluble pigmentresults in the formation of an adduct which can impart the solubility ofthe stabilizing agent in the solvent to the insoluble pigment. In thisadduct, the insoluble pigment strongly interacts with the stabilizingagent. Therefore, the adduct can be isolated as a crystallinesolvent-soluble solid.

[0033] Further, since the coloring material according to the presentinvention requires neither the provision of any complicate step ofdispersion nor the use of any dispersant for a pigment, a mixeddispersion of a plurality of coloring materials and a highlyconcentrated solution thereof can be easily prepared. This facilitatesthe regulation of hue of the coloring material and the like.

[0034] All the soluble pigment precursors disclosed in Japanese PatentLaid-Open No. 188234/1995 or Japanese Patent Laid-Open No. 6242/1996 canbe used in the present invention. Specifically, soluble pigmentprecursors usable in the present invention are those convertible toinsoluble pigments by a chemical, thermal, or photolytic method or byirradiation induction means, more specifically compounds represented byformula (I):

A(B)_(x)  (I)

[0035] wherein x is a number of 1 to 4; A represents a residue ofquinacridone, anthraquinone, perylene, indigo, quinophthalone,isoindolinone, dioxazine, diketopyrrololylol, or a colorant of azoseries. These residues are attached to group Bs, wherein the number ofBs is x, through a nitrogen atom as a part of A. B represents a groupattached to A, and is represented by any one of formulae

[0036] In the formulae (II), (III), and (IV), m, n, and p are eachindependently of one another 0 or 1; X is C₁-C₄ alkylene or C₂-C₈alkenylene; Y is a group -V-(CH₂)_(q)—; Z is a group -V-(CH₂)_(r)—wherein V is C₃-C₆ cycloalkylene; q is 1 to 6; r is a: number of 0 to 6;R₁ and R₂ are each independently of the other hydrogen, C₁-C₆ alkyl,C₁-C₄ alkoxy, halogen, CN, NO₂, unsubstituted phenyl or phenoxy, orphenyl or phenoxy which is substituted by C₁-C₄ alkyl, C₁-C₄ alkoxy, orhalogen; and Q is hydrogen, CN, Si(R₄)₃, a group C(R₅)(R₆)(R₇) whereinR₅, R₆, and R₇ are each independently of one another hydrogen or halogenwith the proviso that at least one of R₅, R₆, and R₇ is halogen,

[0037] a group of formula

[0038] wherein R₁ and R₂ are as defined above, a group SO₂R₅ or SR₈wherein R₈ is C₁-C₄ alkyl, a group CH(R₉)₂ wherein R₉ is unsubstitutedphenyl or phenyl which is substituted by C₁-C₄ alkyl, C₁-C₄ alkoxy, orhalogen, or a group of formula

[0039] R₃ and R₄ are each independently of the other hydrogen, C₁-C₁₈alkyl, or a group of formula

[0040] wherein X, Y, R₁, R₂, m, and n are as defined above, or R₃ andR₄, together with the linking nitrogen atom, form pyrrolidinyl,piperidinyl, or morpholinyl radical; and A(B)_(x) may additionallycontain

[0041] —NH₂ group.

[0042] Further, in addition to the above method, the soluble pigmentprecursor usable in the present invention may also be produced from aninsoluble pigment having a polar group selected from the groupconsisting of primary amines, secondary amines, cyclic amines, and ahydroxyl group.

[0043] Conventional organic compounds, oligomers, or polymers may bepreferably used solely or in a combination of two or more as thestabilizing agent comprising an organic compound having a structure or afunctional group capable of stabilizing the dispersibility of theinsoluble pigment in a solvent according to the present invention, sofar as the stabilizing agent has a group selected from the groupconsisting of >CO, —NH₂, >NH, >N—, ═N⁺<, —CONH₂, —CONH—,—NHCOO—, >NCOO—, —NHCONH—, (—NHCO)₂N—, and —OH.

[0044] The stabilizing agent is preferably characterized by having anamine value, more preferably characterized by having an amine value ofnot less than 1 mg KOH/g and not more than 230 mg KOH/g. Mostpreferably, the stabilizing agent has the above amine value and, at thesame time, a urethane bond. Specific examples of stabilizing agentsinclude acrylic esters, methacrylic esters, vinyl esters, vinylcarbazoleand derivatives thereof, vinylpyrrolidone and derivatives thereof,vinylpyridine and derivatives thereof, acrylamide and derivativesthereof, vinylimidazole and derivatives thereof, ethyleneimine andderivatives thereof, phenol compounds and derivatives thereof, urea andmodified ureas, melamine, amides, amide-imide and derivatives thereof,amino acids, and urethane compounds, and oligomers or polymers of theabove compounds. They may be used solely or in a combination of two ormore.

[0045] Further, the stabilizing agent according to the presentinvention, after the introduction of a reactive double bond group, mayalso be used as a binder component which is used to form a coatingfollowed by polymerization with other monomer or reactive polymer. Atthat time, the amount of the reactive double bond group introduced ispreferably in the range of 0.1 to 20 per molecule on average.

[0046] The soluble pigment precursor and the stabilizing agent are mixedtogether in a weight ratio of 0.01:99.99 to 80:20, preferably in aweight ratio of 1:99 to 70:30, more preferably in a weight ratio of 5:95to 60:40, most preferably in a weight ratio of 10:90 to 50:50.

[0047] Examples of suitable solvents usable herein include: ethers, suchas tetrahydrofuran and dioxane; glycol ethers, such as ethylene glycolmethyl ether, ethylene glycol ethyl ether, diethylene glycol monomethylether, and diethylene glycol monoethyl ether; aprotic solvents, such asacetonitrile, benzonitrile, N,N-dimethylformamide, nitrobenzene,N-methylpyrrolidone, halogenated aliphatic or aromatic hydrocarbons,such as trichloromethane, unsubstituted or alkyl-, alkoxy- orhalogen-substituted benzene, such as xylene, anisole, and chlorobenzene,and aromatic N-heterocyclic compounds, such as pyridine, picoline, orquinoline; alcohols, such as methanol, ethanol, isobutanol, propyleneglycol, and diacetone alcohol; carboxylic esters and lactones, such aspropylene carbonate, ethyl acetate, butyl acetate, methoxypropylacetate, methyl propionate, ethyl benzoate, γ-butyrolactone, andγ-valerolactone; sulfoxides, such as dimethyl suloxide; sulfones, suchas dimethyl sulfone and diethyl sulfone; and ketones, such as dimethylketone, methyl ethyl ketone, cyclopentanone, and cyclohexanone. Further,monomers having various reactive functional groups may also be used. Thecoloring material according to the present invention is preferablyregulated using one of or a mixture of the above-described solvents to asolid content of 1 to 90% by weight, preferably 5 to 80% by weight, morepreferably 10 to 70% by weight, most preferably 20 to 60% by weight,based on the solution.

[0048] The soluble pigment precursor may be converted to an insolublepigment by the addition of an acid, the addition of a base, byirradiation with an electromagnetic radiation, an electron beam, or aneutron, and/or by heating. The coloring material produced by conversionof the soluble pigment precursor to the insoluble pigment, even when asolution prepared by dissolving the soluble pigment precursor in asolvent to saturation is used, can be concentrated without causingnoticeable precipitate. In general, the solution thus produced does notexhibit properties inherent in the pigment in such a state that thesolution is coated on a suitable substrate. Although the reason for thishas not been fully elucidated, the reason is believed to reside in thatthe insoluble pigment and the stabilizing agent interact with each otheron a molecular level to form an adduct and, in this state, are stablypresent in the matrix. Further, in some cases, they come to haveproperties inherent in the pigment through a chemical reaction utilizingan acid or a base produced from various additives, irradiation with anelectromagnetic radiation, for example, visible light, UV (ultravioletlight), laser beams, X-rays, electron beams, or neutrons, and/orheating.

[0049] The coloring material according to the present invention may beused as plastic materials, melts, spinning solutions, paint systems,positive- or negative-working UV resists, positive- or negative-workingelectron beam resists, coating materials, printing inks, for example,for screen printing, gravure printing, flexography, or offset printing,non-impact printing inks, for example, for ink jet printing or thermaltransfer printing, toners, and coloring materials as compositions,particularly as color filters for liquid crystal displays using aresist.

[0050] In the production of color filters, a suitable binder componentis used in combination with photolithography, ink jet recording,electrodeposition, sublimation dye thermal transfer recording (thermaldye transfer recording) or the like. The coloring material according tothe present invention can be advantageously used in all of these cases.

[0051] Second Invention

[0052] The color filter according to the second invention ischaracterized by comprising a colored layer as colored pixels providedon a transparent substrate, said colored layer containing a coloringmaterial, said coloring material being produced by providing a solutioncomprising (1) a soluble pigment precursor which is convertible into aninsoluble pigment, (2) a solvent capable of dissolving the solublepigment precursor therein, and (3) a stabilizing agent comprising anorganic compound having a structure or a functional group capable ofstabilizing the dispersibility of the insolubilized pigment in thesolvent, and converting said soluble pigment precursor into an insolublepigment.

[0053] The color filter according to another aspect of the presentinvention is characterized by comprising a colored layer as coloredpixels provided on a transparent substrate, said colored layercontaining a coloring material, said coloring material comprising anadduct formed by interaction between (1) an insoluble pigment producedby conversion from a soluble pigment precursor and (2) a stabilizingagent comprising an organic compound having a structure or a functionalgroup capable of stabilizing the dispersibility of the insolubilizedpigment in a solvent.

[0054] The colored layer referred to herein is formed of a transparentresin with an insoluble pigment produced from the coloring materialbeing dispersed therein. The transparent resin may be a positive- ornegative-working resist resin, a positive- or negative-workingUV-curable resist, a positive- or negative-working electron beam-curableresist, or a polymer or a prepolymer. The transparent resin may containa stabilizing agent comprising an organic compound having a structure ora functional group capable of stabilizing the dispersibility of aninsolubilized pigment in the solvent. The stabilizing agent may be anyof the positive- or negative-working resist resin, the positive- ornegative-working UV-curable resist, the positive- or negative-workingelectron beam-curable resist, and the polymer or the prepolymer.

[0055] The coloring material used in the present invention may beproduced by dissolving, in a solvent to saturation, an organic compoundhaving a structure or a functional group capable of stabilizing thedispersibility of an insolubilized pigment in the solvent and a solublepigment precursor convertible into an insoluble pigment and applyingchemical means, thermal means, photolytic means, radiation inducedmeans, or means comprising a combination of two or more of the abovemeans to convert at least a part of the precursor to a pigment.

[0056] By virtue of the presence of the organic compound having astructure or a functional group capable of stabilizing thedispersibility of an insolubilized pigment in the solvent, the coloringmaterial, even when concentrated after the conversion of the solubleprecursor to the pigment, is free from any precipitate and anysignificant floating matter. Therefore, a highly concentrated dispersionof the soluble precursor, at least a part of which has been converted toa pigment, can be easily realized. This can overcome the above problemscaused by conversion to an insoluble pigment, for example, after coatingformation.

[0057] The coloring material used in the present invention, even whenconcentrated, is stably present. When the coloring material is furtherconcentrated, the coloring material is precipitated as solid matter.This solid matter is sometimes crystalline, can be easily isolated fromthe dispersion, and as such can be stably stored for a long period oftime. The isolation of the solid matter from the dispersion permitsimpurities, such as excess stabilizing agent, to be easily removed, forexample, by washing.

[0058] Further, the solidified coloring material, together with asolvent in which an insoluble pigment per se cannot be easily dispersed,can easily constitute a stable dispersion or a highly concentratedsolution thereof without providing any complicate step of dispersion oruse of any dispersant for a pigment.

[0059] Although the reason for this has not been fully elucidated, thereason is believed to reside in that, in the course of conversion of thesoluble pigment precursor into the insoluble pigment, interaction on amolecular level between the stabilizing agent and the insoluble pigmentresults in the formation of an adduct which can impart the solubility ofthe stabilizing agent in the solvent to the insoluble pigment. In thisadduct, the insoluble pigment strongly interacts with the stabilizingagent. Therefore, the adduct can be isolated as a crystallinesolvent-soluble solid.

[0060] Further, since this coloring material requires neither theprovision of any complicate step of dispersion nor the use of anydispersant for a pigment, a mixed dispersion of a plurality of coloringmaterials and a highly concentrated solution thereof can be easilyprepared. This facilitates the regulation of hue of the coloringmaterial and the like.

[0061] All the soluble pigment precursors described in Japanese PatentLaid-Open No. 188234/1995 or Japanese Patent Laid-Open No. 6242/1996 canbe used in the present invention. Specifically, soluble pigmentprecursors usable in the present invention are those convertible toinsoluble pigments by a chemical, thermal, or photolytic method or byirradiation induction means, more specifically compounds represented byformula (I):

A(B)_(x)  (I)

[0062] wherein x is a number of 1 to 4; A represents a residue ofquinacridone, anthraquinone, perylene, indigo, quinophthalone,isoindolinone, dioxazine, diketopyrrololylol, or a colorant of azoseries. These residues are attached to group Bs, wherein the number ofBs is x, through a nitrogen atom as a part of A. B represents a groupattached to A, and is represented by any one of formulae

[0063] In the formulae (II), (III), and (IV), m, n, and p are eachindependently of one another 0 or 1; X is C₁-C₄ alkylene or C₂-C₈alkenylene; Y is a group -V-(CH₂)_(q)—; Z is a group -V-(CH₂)_(r)—wherein V is C₃-C₆ cycloalkylene; q is 1 to 6; r is a number of 0 to 6;R₁ and R₂ are each independently of the other hydrogen, C₁-C6 alkyl,C₁-C₄ alkoxy, halogen, CN, NO₂, unsubstituted phenyl or phenoxy, orphenyl or phenoxy which is substituted by C₁-C₄ alkyl, C₁-C₄ alkoxy, orhalogen; and Q is hydrogen, CN, Si(R₄)₃, a group C(R₅)(R₆)(R₇) whereinR₅, R₆, and R₇ are each independently of one another hydrogen or halogenwith the proviso that at least one of R₅, R₆, and R₇ is halogen,

[0064] a group of formula

[0065] wherein R₁ and R₂ are as defined above,

[0066] a group SO₂R₈ or SR₈ wherein R₈ is C₁-C₄ alkyl,

[0067] a group CH(R₉)₂ wherein R₉ is unsubstituted phenyl or phenylwhich is substituted by C₁-C₄ alkyl, C₁-C₄ alkoxy, or halogen, or agroup of formula

[0068] R₃ and R₄ are each independently of the other hydrogen, C₁-C₁₈alkyl, or a group of formula

[0069] wherein X, Y, R₁, R₂, m, and n are as defined above, or R₃ andR₄, together with the linking nitrogen atom, form pyrrolidinyl,piperidinyl, or morpholinyl radical; and A(B)_(x) may additionallycontain

[0070] —NH₂ group.

[0071] Further, in addition to the above method, the soluble pigmentprecursor usable in the present invention may also be produced from aninsoluble pigment having a polar group selected from the groupconsisting of primary amines, secondary amines, cyclic amines, and ahydroxyl group.

[0072] Conventional organic compounds, oligomers, or polymers may bepreferably used solely or in a combination of two or more as thestabilizing agent comprising an organic compound having a structure or afunctional group capable of stabilizing the dispersibility of theinsoluble pigment in a solvent according to the present invention, sofar as the stabilizing agent has a group selected from the groupconsisting of >CO, —NH₂, >NH, >N—, ═N⁺<, —CONH₂, —CONH—,—NHCOO—, >NCOO—, —NHCONH—, (—NHCO)₂N—, and —OH.

[0073] The stabilizing agent is preferably characterized by having anamine value, more preferably characterized by having an amine value ofnot less than 1 mg KOH/g and not more than 230 mg KOH/g. Mostpreferably, the stabilizing agent has the above amine value and, at thesame time, a urethane bond. Specific examples of stabilizing agentsinclude acrylic esters, methacrylic esters, vinyl esters, vinylcarbazoleand derivatives thereof, vinylpyrrolidone and derivatives thereof,vinylpyridine and derivatives thereof, acrylamide and derivativesthereof, vinylimidazole and derivatives thereof, ethyleneimine andderivatives thereof, phenol compounds and derivatives thereof, urea andmodified ureas, melamine, amides, amide-imide and derivatives thereof,amino acids, and urethane compounds, and oligomers or polymers of theabove compounds. They may be used solely or in a combination of two ormore.

[0074] Further, the stabilizing agent, after the introduction of areactive double bond group thereinto, may also be used as a bindercomponent which is used to form a coating followed by polymerizationwith other monomer or reactive polymer. At that time, the amount of thereactive double bond group introduced is preferably in the range of 0.1to 20 per molecule on average.

[0075] The soluble pigment precursor and the stabilizing agent are mixedtogether in a weight ratio of 0.01:99.99 to 80:20, preferably in aweight ratio of 1:99 to 70:30, more preferably in a weight ratio of 5:95to 60:40, most preferably in a weight ratio of 10:90 to 50:50.

[0076] Examples of suitable solvents usable herein include: ethers, suchas tetrahydrofuran and dioxane; glycol ethers, such as ethylene glycolmethyl ether, ethylene glycol ethyl ether, diethylene glycol monomethylether, and diethylene glycol monoethyl ether; aprotic solvents, such asacetonitrile, benzonitrile, N,N-dimethylformamide, nitrobenzene,N-methylpyrrolidone, halogenated aliphatic or aromatic hydrocarbons,such as trichloromethane, unsubstituted or alkyl-, alkoxy- orhalogen-substituted benzene, such as xylene, anisole, and chlorobenzene,and aromatic N-heterocyclic compounds, such as pyridine, picoline, orquinoline; alcohols, such as methanol, ethanol, isobutanol, propyleneglycol, and diacetone alcohol; carboxylic esters and lactones, such aspropylene carbonate, ethyl acetate, butyl acetate, methoxypropylacetate, methyl propionate, ethyl benzoate, γ-butyrolactone, andγ-valerolactone; sulfoxides, such as dimethyl suloxide; sulfones, suchas dimethyl sulfone and diethyl sulfone; and ketones, such as dimethylketone, methyl ethyl ketone, cyclopentanone, and cyclohexanone. Further,monomers having various reactive functional groups may also be used. Thecoloring material according to the present invention is preferablyregulated using one of or a mixture of the above-described solvents to asolid content of 1 to 90% by weight, preferably 5 to 80% by weight, morepreferably 10 to 70% by weight, most preferably 20 to 60% by weight,based on the solution.

[0077] The soluble pigment precursor may be converted to an insolublepigment by the addition of an acid, the addition of a base, byirradiation with an electromagnetic radiation, an electron beam, or aneutron, and/or by heating. The coloring material produced by conversionof the soluble pigment precursor to the insoluble pigment, even when asolution prepared by dissolving the soluble pigment precursor in asolvent to saturation is used, can be concentrated without causingnoticeable precipitate. In general, the solution thus produced does notexhibit properties inherent in the pigment in such a state that thesolution is coated on a suitable substrate. Although the reason for thishas not been fully elucidated, the reason is believed to reside in thatthe insoluble pigment and the stabilizing agent interact with each otheron a molecular level to form an adduct and, in this state, are stablypresent in the matrix. Further, in some cases, they come to haveproperties inherent in the pigment through a chemical reaction utilizingan acid or a base produced from various additives, irradiation with anelectromagnetic radiation, for example, visible light, UV (ultravioletlight), laser beams, X-rays, electron beams, or neutrons, and/orheating.

[0078] The color filter according to the present invention ischaracterized in that colored pixels are constituted by a colored layerformed of a transparent resin with an insoluble pigment produced fromthe coloring material being dispersed therein.

[0079] The particle diameter of the insoluble pigment produced by theabove method is not more than the wavelength of incident light, that is,in the range of 1 nm to 300 nm in terms of average particle diameter,and, at the same time, the particle diameter distribution of the pigmentfalls within a specific range, that is, is within ±30% of the averageparticle diameter. By virtue of this, a lowering in transmittance causedby light scattering can be effectively suppressed, and, in its turn, amuch improvement in transparency of the formed colored pixels can beattained over the transparency of colored pixels obtained usingconventional pigment-dispersed systems.

[0080] Further, the insoluble pigment produced from the coloringmaterial has excellent display quality, and thus can easily form coloredpixels which have ideal spectral characteristics as a color filter,specifically have a spectral characteristic curve in a visible regionsuch that the light transmittance in a light absorption region is in therange of 0 to 20% while the light transmittance in a light transmissionregion is not less than 50%.

[0081] The amount of the insoluble pigment produced from the coloringmaterial can be regulated by regulating the solid content of the matrix,specifically can be regulated in the range of 10 to 90% by weight interms of the content of the insoluble pigment on a solid basis in thecolored pixels of the color filter, and, thus, the insoluble pigment canbe easily used in higher concentration. Therefore, the contrast can alsobe significantly improved over the contrast attained in the conventionalpigment-dispersed system, and can be set, for example, at not less than2,000.

[0082] According to the present invention, the formation of a coloredlayer comprising an insoluble pigment, produced from the coloringmaterial, dispersed in a transparent resin can constitute a color filterfor use in liquid crystal displays, various solid-state image sensingdevices, color video cameras or the like.

[0083] More specifically, a composition containing a coloring materialis coated on a substrate for constituting a color filter by coatingmeans, such as a spinner, a roll coater, a dip coater, or a bar coater,to a coating thickness of about 0.1 to 10 μm on a dry basis to form acolored layer.

[0084] Further, desired colored layers of a plurality of colors may beformed by predetermined patterning to prepare a color filter.

[0085] In the production of color filters, a suitable binder componentis used in combination with photolithography, ink jet recording,electrodeposition, sublimation dye thermal transfer recording (thermaldye transfer recording) or the like. The coloring material according tothe present invention can be advantageously used in all of these cases.

[0086] In general, for example, a color filter for TFT comprises: aglass substrate; and, provided on the glass substrate, a black portionfor light shielding, each colored portion of RGB for color display, atransparent protective layer for protecting these colored layers, and atransparent conductive layer for driving a liquid crystal.

[0087] Photosensitive resin compositions usable in the production ofcolor filters include, for example, those disclosed in U.S. Pat. No.3,549,367, such as a photopolymerizable unsaturated monomer comprisingan addition polymerizable unsaturated monomer, a photopolymerizationinitiator, and a binder, a photopolymerizable photosensitivecomposition, and a photocrosslinkable photopolymer having an unsaturateddouble bond reside on its main chain or side chain. The additionpolymerizable unsaturated monomer contained in the photopolymerizablephotosensitive composition is preferably a compound which has at leastone addition polymerizable ethylenically unsaturated group and has aboiling point of 100° C. or above at normal pressure. Specific examplesof such compounds include monofunctional acrylates and methacrylates andcompound produced by adding ethylene oxide or propylene oxide topolyfunctional alcohols and then methacrylating the addition product.Additional examples of addition polymerizable unsaturated monomersusable herein include polyfunctional acrylates or methacrylates, such aspolyester acrylates and epoxy acrylates produced by reacting an epoxyresin with methacrylic acid, photocurable monomers and oligomers,butyral resins, styrene-maleic acid copolymers, polyvinyl acetate, andphenolic resins. The amount of the photopolymerizable component used ispreferably about 5 to 50% by weight.

[0088] Photopolymerization initiators include conventional compounds,for example, vicinal polyketoaldonyl compounds, α-carbonyl compounds,asioin ethers, various quinone compounds, a combination oftriallylimidazole dimer with p-aminophenyl ketone, and trioxadiazolecompounds. Particularly preferred is2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone (Irgacure 369,manufactured by Chiba Geigy).

[0089] The binder is preferably linear organic high-molecular weightpolymers which are compatible with the above monomers, soluble inorganic solvents, and developable with an aqueous weakly alkalinesolution. More specifically, methacrylic acid copolymers, acrylic acidcopolymers, itaconic acid copolymers, crotonic acid copolymers, maleicacid copolymers, partially esterified maleic acid copolymers and thelike may be used. In addition, water-soluble polymers may also be used.Further, alcohol-soluble nylon and the like may be used from theviewpoint of improving the strength of the cured layer. The content ofthe binder component is suitably less than 90% by weight, preferably 30to 85% by weight. Further, if necessary, thermal polymerizationinhibitors may also be added.

[0090] Suitable organic solvents for the photosensitive resincomposition usable herein include glycol ether compounds, acetatesthereof, acetic ester compounds, and ketone compounds. The concentrationof the solution is suitably not more than 70%, preferably 15 to 50%.

[0091] According to a preferred embodiment of the present invention, thephotosensitive resin composition with the coloring material dispersedtherein is provided, and coated on a substrate, followed by exposure andthen development to perform patterning. This procedure can be repeatedthree times in total respectively for R, G, and B to prepare apredetermined color filter.

[0092] Third Invention

[0093] The coloring material according to the third invention ischaracterized by comprising a specific pyrrole derivative represented byformulae (I) to (V) described later.

[0094] The coloring material according to the present invention containsa pyrrolo[3,4-c]pyrrole derivative produced by converting at least oneketopyrrole group in a pyrrolo[3,4-c]pyrrole of formula

[0095] wherein A and B are each independently of the other a group offormula

[0096] wherein R₁ and R₂ are each independently of the other hydrogen,halogen, C₁—C₁₈ alkyl, C₁-C₁₈ alkoxy, C₁-C₁₈ alkylmercapto, C₁-C₁₈alkylamino, —CN, —NO₂, phenyl, trifluoromethyl, C₅-C₆ cycloalkyl,—C═N—(C₁-C₁ alkyl), a group of formula

[0097] imidazolyl, pyrrazolyl, triazolyl, piperazinyl, pyrrolyl,oxazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, morpholinyl,piperidinyl, or pyrrolidinyl; G is —CH₂—, —CH(CH₃)—, —CH(CH₃)₂—, —CH═N—,—N═N—, —O—, —S—, —SO—, —SO—, or —NR₇—; R₃ and R₄ are each independentlyof the other hydrogen, halogen, C₁-C₁₈ alkoxy, or —CN; R₅ and R₆ areeach independently of the other hydrogen, halogen, or C₁-C₆ alkyl; andR₇ is hydrogen or C₁-C₆ alkyl; and

[0098] D and E are each independently of the other a group of formula

[0099] wherein, in the formulae (II), (III), and (IV), m, n, and p areeach independently of one another a number of 0 or 1; X is C₁-C₁₄alkylene or C₂-C₆ alkenylene; Y is a group -V-(CH₂)_(q)—; Z is a group-V-(CH₂)_(r)—; V is C₃-C₆ cycloalkylene; q is an integer from 1 to 6; ris an integer from 0 to 6; R₈ and R₉ are each independently of the otherhydrogen, C₁-C₆ alkyl, C₁-C₄ alkoxy, halogen, CN, NO₂, unsubstitutedphenyl or phenoxy, or phenyl or phenoxy which is substituted by C₁-C₄alkyl, C₁-C₄ alkoxy, or halogen; and Q is hydrogen, CN, Si(R₈)₃, a groupC(R₁₂)(R₁₃)(R₁₄) wherein R₁₂, R₁₃, and R₁₄ are halogen, a group offormula

[0100] wherein R₈ and R₉ are as defined above,

[0101] a group SO₂R₁₅ or SR₁₅ wherein R₁₅ represents phenyl which issubstituted by a C₁-C₄ alkyl, a C₁-C₄ alkoxy, or a halogen, or a groupof formula

[0102] R₁₀ and R₁₁ are each independently of the other hydrogen, C₁-C₂₀alkyl, or a group of formula

[0103] wherein X, Y, R₈, R₉, m, and n are as defined above, or R₁₀ andR₁₁, together with the linking nitrogen atom, form pyrrolidinyl,piperidinyl, or morpholinyl radical; and D may be hydrogen, with theproviso that, if D and/or E are a group of formula (III), Q is hydrogen,and n is 0, m must be 1 and X must be a C₂-C₁₄ alkylene or C₂-C₈alkenylene group which is branched at the carbon atom attached to theoxygen atom,

[0104] said at least one ketopyrrole group being converted to

[0105] wherein A may be B with the proviso that, if A is B, D is E; andR′ is C₁-C₅ alkyl.

[0106] In this case, A and B in formula (V) are preferably eachindependently of the other a group of formula

[0107] wherein R₁ and R₂ are each independently of the other hydrogen,chloro, bromo, C₁-C₄ alkyl, C₁-C₆alkoxy, C₁-C₆ alkylamino, CN, orphenyl; G is —O—, —NR₇—, —N═N—, or —SO₂—; R₇ is hydrogen, methyl, orethyl; and R₃ and R₄ are hydrogen.

[0108] According to a preferred embodiment of the present invention, Aand B in formula (V) are identical to each other.

[0109] Further, according to another preferred embodiment of the presentinvention, A and B in formula (V) are a group of formula

[0110] wherein R₁ and R₂ are each independently of the other hydrogen,methyl, tert-butyl, chloro, bromo, CN, or phenyl.

[0111] According to another embodiment, in the coloring materialcontaining a pyrrolo[3,4-c]pyrrole derivative according to claim 1, D ishydrogen or E, and E is a group of formula

[0112] or formula (IV) wherein, in formulae (VI), (VII), and (IV), m is0 or 1; X is C₁-C₄ alkylene or C₁-C₅ alkenylene; R₈ and R₉ are eachindependently of the other hydrogen, C₁-C₄ alkyl, methoxy, chloro, or—NO₂—; Q is hydrogen, CN, CCl₃, a group of formula

[0113] wherein R₈ and R₉ are as defined above,

[0114] SO₂, SH₃, or SCH₃; R₁₀ and R₁₁ are each independently of theother hydrogen, C₁-C₄ alkyl, or a group of formula

[0115] or R₁₀ and R₁₁, taken together, form a piperidinyl radical, withthe proviso that, if D and/or E are a group of formula (IX) and Q ishydrogen, X must be a group of formula

[0116] Further, a pyrrolo[3,4-c]pyrrole derivative, wherein D and E informula (V) are identical to each other and are a group of formula

[0117] also falls within the scope of the present invention.

[0118] The pyrrolo[3,4-c]pyrrole derivative of formula (V) may beproduced by reacting a pyrro[3,4-c]pyrrole of formula (I) in a solventincluding a lower alcohol and in the presence of a base as a catalystpreferably at a temperature of 0 to 400° C., more preferably at atemperature of 20 to 200° C., for 2 to 80 hr.

[0119] Pyrrolo[3,4-c]pyrrole compounds of formula (I) are disclosed indetail in Japanese Patent Laid-Open No. 188234/1995, the disclosure ofwhich is incorporated herein by reference.

[0120] The coloring material according to the present invention containsa pyrrolo[3,4-c]pyrrole derivative of formula (V).

[0121] The coloring material according to the present invention embracesa coloring material which contains as its component apyrrolo[3,4-c]pyrrole of formula

[0122] wherein A and B are as defined in formula (I),

[0123] which has been produced in situ by thermal decomposition,photolysis, or chemical decomposition of the pyrrolo[3,4-c]pyrrolederivative of formula (I).

[0124] According to the present invention, the formation of a coloredlayer comprising an insoluble pigment, produced from the coloringmaterial, dispersed in a transparent resin can constitute a color filterfor use in liquid crystal displays, various solid-state image sensingdevices, color video cameras or the like.

[0125] More specifically, a composition containing a coloring materialis coated on a substrate for constituting a color filter by coatingmeans, such as a spinner, a roll coater, a dip coater, or a bar coater,to a coating thickness of about 0.1 to 10 μm on a dry basis to form acolored layer.

[0126] Further, desired colored layers of a plurality of colors may beformed by predetermined patterning to prepare a color filter.

[0127] In the production of color filters, a suitable binder componentis used in combination with photolithography, ink jet recording,electrodeposition, sublimation dye thermal transfer recording (thermaldye transfer recording) or the like. The coloring material according tothe present invention can be favorably used in all of these cases.

[0128] In general, for example, a color filter for TFT comprises: aglass substrate; and, provided on the glass substrate, a black portionfor light shielding, each colored portion of RGB for color display, atransparent protective layer for protecting these colored layers, and atransparent conductive layer for driving a liquid crystal.

[0129] Photosensitive resin compositions usable in the production ofcolor filters include, for example, those disclosed in U.S. Pat. No.3,549,367, such as a photopolymerizable unsaturated monomer comprisingan addition polymerizable unsaturated monomer, a photopolymerizationinitiator, and a binder, a photopolymerizable photosensitivecomposition, and a photocrosslinkable photopolymer having an unsaturateddouble bond reside on its main chain or side chain. The additionpolymerizable unsaturated monomer contained in the photopolymerizablephotosensitive composition is preferably a compound which has at leastone addition polymerizable ethylenically unsaturated group and has aboiling point of 100° C. or above at normal pressure. Specific examplesof such compounds include monofunctional acrylates and methacrylates andcompound produced by adding ethylene oxide or propylene oxide topolyfunctional alcohols and then methacrylating the addition product.Additional examples of addition polymerizable unsaturated monomersusable herein include polyfunctional acrylates or methacrylates, such aspolyester acrylates and epoxy acrylates produced by reacting an epoxyresin with methacrylic acid, photocurable monomers and oligomers,butyral resins, styrene-maleic acid copolymers, polyvinyl acetate, andphenolic resins. The amount of the photopolymerizable component used ispreferably about 5 to 50% by weight.

[0130] Photopolymerization initiators include conventional compounds,for example, vicinal polyketoaldonyl compounds, α-carbonyl compounds,asioin ethers, various quinone compounds, a combination oftriallylimidazole dimer with p-aminophenyl ketone, and trioxadiazolecompounds. Particularly preferred is2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone (Irgacure 369,manufactured by Chiba Geigy).

[0131] The binder is preferably linear organic high-molecular weightpolymers which are compatible with the above monomers, soluble inorganic solvents, and developable with an aqueous weakly alkalinesolution. More specifically, methacrylic acid copolymers, acrylic acidcopolymers, itaconic acid copolymers, crotonic acid copolymers, maleicacid copolymers, partially esterified maleic acid copolymers and thelike may be used. In addition, water-soluble polymers may also be used.Further, alcohol-soluble nylon and the like may be used from theviewpoint of improving the strength of the cured layer. The content ofthe binder component is suitably less than 90% by weight, preferably 30to 85% by weight. Further, if necessary, thermal polymerizationinhibitors may also be added.

[0132] Suitable organic solvents for the photosensitive resincomposition usable herein include glycol ether compounds, acetatesthereof, acetic ester compounds, and ketone compounds. The concentrationof the solution is suitably not more than 70%, preferably 15 to 50%.

[0133] According to a preferred embodiment of the present invention, thephotosensitive resin composition with the coloring material dispersedtherein is provided, and coated on a substrate, followed by exposure andthen development to perform patterning. This procedure is repeated threetimes in total respectively for R, G, and B to prepare a predeterminedcolor filter.

EXAMPLES

[0134] The present invention will be described in more detail withreference to the following examples. In the following examples, all“parts” are by weight, and all “%” are by weight.

Example A1

[0135] (1) Preparation of Solution

[0136] 4 parts ofN,N′-bis-tert-amyloxycarbonyl-1,4-diketo-3,6-di(4′-chlorophenyl)pyrrolo-[3,4-c]pyrrole(DPP) was dissolved in 76 parts of methoxypropyl acetate (PGMEA) whichhad been dried over Molecular Sieves 4A. The solution was filteredthrough a 0.1-μm filter. To this solution was added a solution of 1.36parts of Disperbyk-164 (manufactured by Bik-Chemie Japan K.K., solidcontent 60%, amine value 18 mg KOH/g) in 1.64 parts of PGMEA. Themixture was stirred at room temperature to prepare a transparent orangesolution.

[0137] (2) Preparation of Concentrated Solution

[0138] 0.32 part of a 10% hydrochloric acid-methanol solution dissolvedin a minor amount of PGMEA was added dropwise to and mixed with thesolution prepared in (1) over a period of one hr at a temperature of 40°C. The mixture was stirred for additional one hr. The resultant solutionwas a transparent fluorescent yellow solution. This solution wasconcentrated at a temperature of 40° C. in vacuo to bring the totalamount of the solution to 40 parts. The concentrated solution was freefrom precipitates and was a transparent orange solution.

[0139] (3) Identification by Thin-Layer Chromatography

[0140] The solution prepared in (1), the concentrated solution preparedin (2), and a solution of 0.5 part of DPP in 4.5 parts of PGMEA weredeveloped with cyclohexane cyclohexanone=7:3. As a result, a single spotappeared at rf=0.8 for the solution prepared in (1) and the solution ofDPP in PGMEA, and at rf=0.7 for the concentrated solution prepared in(2).

[0141] (4) Isolation of Solidified Coloring Material

[0142] The concentrated solution prepared in (2) was allowed to stand toprecipitate yellow crystals which were then collected, followed byrecrystallization. The purified product was then dried in vacuoovernight to prepare a solidified coloring material. A ¹H-NMR spectrumchart for the solidified coloring material thus obtained is shown inFIG. 1. The solubility of the isolated solidified coloring material insolvents was 10% by weight for PGMEA, 15% by weight for cyclohexane, 10%by weight for chloroform, and 5% by weight for ethyl acetate. Thesolubility of DPP in solvents was 5% by weight for PGMEA, 10% by weightfor cyclohexanone, 10% by weight for chloroform, and not more than 1% byweight for ethyl acetate. Thus, there was a difference in solubilityamong the solvents.

[0143] Further, a solution prepared by redissolving the isolatedsolidified coloring material in cyclohexanone was free from precipitatesand stable even when the solid content exceeded 15% by weight.

[0144] (5) Preparation of Coating Solution and Coating

[0145] 10 parts by weight of a phenolic resin (polyvinylphenol PHM-C,manufactured by Maruzen Petrochemical Co., Ltd.) was dissolved in andmixed with 100 parts by weight of a 10 wt % clear solution prepared byredissolving the solidified coloring material prepared in (4) in PGMEA.The coating liquid thus obtained was filtered through a 0.1-μm filter,and then coated by means of a spin coater on a glass substrate of 5 cm×5cm with a thickness of 1.1 mm. The coated substrate was dried at roomtemperature for 30 min and on a hot plate of 90° C. for one min. Thisdye coating was heated in an oven of 200° C. for 5 min. Thus, a redpigment coating having high transmittance was prepared.

[0146] (6) Evaluation of Coating

[0147] For the red coating prepared in (5), the content of the insolublepigment was 30% by weight on a solid basis, and the light transmittancewas not more than 10% in a light absorption region at not more than 570nm, and was not less than 87% in a light transmission region at not lessthan 620 nm. The contrast ratio was measured, and found to be 3,600. Anattempt has been made to mechanically disperse the same pigment as usedin the red coating with the aid of a dispersant. As a result, thepigment could not be dispersed at all, and any coating could not beformed.

[0148] The size of the insoluble pigment particles in the red coatingprepared in (5) was measured based on a sectional transmission electronphotomicrograph of the coating. As a result, it was found that theaverage particle diameter was 10 nm with the particle size distributionbeing within ±20%, that is, in the range of 8 to 12 nm.

Comparative Example A1

[0149] The solution prepared in (1) of Example Al was concentrated invacuo at a temperature of 40° C. without adding hydrochloric acid untilthe total amount of the solution became 2.5 parts. Precipitates werefound in the concentrated solution. The comparison of this result withthe result of Example A1 reveals that the step of conversion to apigment is necessary to provide a highly concentrated solution.

Comparative Example A2

[0150] A solution was prepared in the same manner as in (1) of ExampleA1, except that a solution of 0.013 part of Disperbyk-180 (solid content79%, amine value 96 mg KOH/g, acid value 95 mg KOH/g), instead ofDisperbyk-164, in 0.1 part of PGMEA was added followed by stirring atroom temperature to prepare a transparent orange solution. 0.04 part ofa 10% hydrochloric acid-methanol solution was added dropwise to andmixed with this solution. The mixture was stirred at a temperature of40° C. for one hr. Orange precipitates were found in the resultantsolution.

Comparative Example A3

[0151] A solution was prepared in the same manner as in (1) of ExampleAl, except that a solution of 0.019 part of Disperbyk-110 (solid content52%, acid value 95 mg KOH/g), instead of Disperbyk-164, in 0.1 part ofPGMEA was added followed by stirring at room temperature to prepare atransparent orange solution. 0.04 part of a 10% hydrochloricacid-methanol solution was added dropwise to and mixed with thissolution. The mixture was stirred at a temperature of 40° C. for one hr.Orange precipitates were found in the resultant solution.

[0152] Thus, according to the present invention, in dissolving (1) asoluble pigment precursor, which is convertible into an insolublepigment, in (2) a solvent capable of dissolving the soluble pigmentprecursor therein, (3) a stabilizing agent, comprising an organiccompound having a structure or a functional group capable of stabilizingdispersibility of the insolubilized pigment in the solvent, is allowedto further exist, and, in this system, the soluble pigment precursor isconverted into an insoluble pigment. By virtue of this, the coloringmaterial, even when concentrated after the conversion of the solubleprecursor apt to constitute an unstable system to the pigment, is freefrom any precipitate and any significant floating matter. Therefore, thepreparation of a highly concentrated solution of the soluble precursor,a part of which has been converted to an insoluble pigment, can beeasily realized. This can overcome the above problems caused byconversion to a (insoluble) pigment, for example, after coatingformation.

[0153] Further, this coloring material, upon removal of the solvent, canbe collected as a crystallized solid. This solidified product can beeasily redissolved in a solvent to prepare a stable highly concentratedsolution from which impurities have been removed as much as possible.

[0154] The coloring material having the above properties according tothe present invention can easily form a pigment-dispersed polymer layerwhich contains a pigment in high concentration and has excellent coatingsmoothness. This makes it possible to apply the coloring material tocolor filters having improved spectral characteristics (higher colorpurity, higher transmittance, and higher contrast) as compared withcolor filters using conventional coloring materials.

[0155] Further, according to the present invention, an organic material,which has a specific structure or functional group having affinity for asoluble pigment precursor and/or a (insoluble) pigment in a medium suchas a solvent, and a soluble pigment precursor are dissolved in a mediumto saturation, and, in this state or alternatively through chemical,thermal, photolytic, or radiation induced means, at least a part of theprecursor is converted to a pigment, followed by concentration. In thiscase, by virtue of the presence of the organic material having aspecific structure or functional group having affinity for the solublepigment precursor and/or the (insoluble) pigment in the medium, thecoloring material, even when concentrated after the conversion of thesoluble precursor apt to constitute an unstable system to the pigment,is free from any precipitate and any significant organic matter.Therefore, the preparation of a highly concentrated solution of thesoluble precursor, a part of which has been converted to an insolublepigment, can be easily realized. This can overcome the above problemscaused by conversion to a (insoluble) pigment, for example, aftercoating formation.

[0156] Further, according to the present invention, the coloringmaterial can easily form a pigment-dispersed polymer layer whichcontains a pigment in high concentration and has excellent coatingsmoothness. This makes it possible to provide color filters havingimproved spectral characteristics (higher color purity, highertransmittance, and higher contrast) as compared with color filters usingconventional coloring materials.

Example B1

[0157] (1) Preparation of Suspension

[0158] 0.98 part ofN,N′-bis-tert-amyloxycarbonyl-1,4-diketo-3,6-di(4′-chlorophenyl)pyrrolo[3,4-c]pyrrole(DPP) was added to 100 parts of methanol which had been dried overMolecular Sieves 4A. To this suspension was added 0.12 part of4-dimethylaminopyridine. The mixture was stirred at room temperature toprepare a yellow suspension.

[0159] (2) Preparation of Dissolved Colored Solution

[0160] The suspension prepared in (1) was stirred at a temperature of60° C. for 2 hr. Thus, a clear solution was prepared. Since a very smallamount of a red solid came to precipitate, the red solid was removedthrough a filter. The filtrate thus obtained was an orange clearsolution.

[0161] (3) Isolation of Solidified Coloring Material (Ring Opened LatentPigment)

[0162] The solution prepared in (2) was concentrated in vacuo at atemperature of 40° C. until the total amount of the solution became 30parts. The concentrated solution was cooled in ice to precipitate ayellow solid. The precipitated yellow solid was collected through afilter. The yellow solid was then dried in vacuo at a temperature of 40°C. overnight. Thus, 0.5 part of a yellow powder (compound 1) representedby the following general formula, wherein one ketopyrrole ring of DPPhad been subjected to methanolysis to cleave a bond between N and C═O,was obtained.

[0163] Compound 1

[0164] (4) Identification by Thin-Layer Chromatography

[0165] The suspension prepared in (1), the solution prepared in (2), anda solution of 0.05 part of the compound (compound 1) prepared in (3) in5 parts of tetrahydrofuran (THF), and a solution of 0.05 part of DPP in5 parts of THF were developed with cyclohexane:THF=4:1. As a result, forthe suspension prepared in (1) and the solution of DPP in THF, a singlespot appeared at rf=0.67. For the solution prepared in (2), two spotsappeared, one of which was a large spot at rf=0.6 and the other was athin small spot at rf=0.45. For the solution of the compound prepared in(3) in THF, a single spot appeared at rf=0.6.

[0166] (5) Properties and Solubility of Compound 1

[0167] For compound 1 prepared in (3), a ¹H-NMR spectrum chart is shownin FIG. 2, and a ¹³C-NMR spectrum chart is shown in FIG. 3. Thesolubility of compound 1 in solvents was 50% by weight for chloroform,28.57% by weight for THF, 10% by weight for cyclohexanone, 4.55% byweight for ethyl acetate, 2% by weight for methoxypropyl acetate(PGMEA), and 0.2% by weight for methanol. Thus, there was a differencein solubility among the solvents.

[0168] (6) Preparation of Coating Solution and Coating

[0169] 3.4 parts of Disperbyk-164 (manufactured by Bik-Chemie JapanK.K., solid content 60%, amine value 18 mg KOH/g) and 5 parts of aphenolic resin (polyvinylphenol PHM-C, manufactured by MaruzenPetrochemical Co., Ltd.) were dissolved in and mixed with 100 parts of a10 wt % clear solution prepared by dissolving compound 1 prepared in (3)in THF. The coating liquid thus obtained was filtered through a 0.45-μmfilter, and then coated by means of a spin coater on a glass substrateof 5 cm×5 cm with a thickness of 0.7 mm. The coated substrate was driedat room temperature for 30 min. The coating was then heated in an ovenof 180° C. for 60 min. Thus, a red pigment coating having hightransmittance was prepared.

[0170] (7) Evaluation of Coating

[0171] For the red coating prepared in (6), the content of the insolublepigment was 20% by weight on a solid basis, and the light transmittancewas not more than 10% in a light absorption region at not more than 570nm, and was not less than 87% in a light transmission region at not lessthan 620 nm. The contrast ratio was measured, and found to be 2,500.

[0172] The size of the pigment particles in the red coating prepared in(6) was measured based on a sectional transmission electronphotomicrograph of the coating. As a result, it was found that theaverage particle diameter was 10 nm with the particle size distributionbeing within ±20%, that is, in the range of 8 to 12 nm.

[0173] Comparative Example B1

[0174] The suspension prepared in (1) of Example B1 was stirred at atemperature of 60° C. for 18 hr to prepare a solution which was thentreated in the same manner as in (3). As a result, a yellow powder(compound 2) represented by the following general formula was obtained.

[0175] Compound 2

[0176] Compound 2 was dissolved in THF, and developed in the same manneras in (4). As a result, a single spot appeared at rf=0.45. For compound2, a ¹H-NMR spectrum chart is shown in FIG. 4, and a ¹³C-NMR spectrumchart is shown in FIG. 5. The solubility of compound 2 in solvents was2% by weight for chloroform, 12.5% by weight for THF, 5% by weight forcyclohexanone, 1% by weight for ethyl acetate, 0.67% by weight formethoxypropyl acetate (PGMEA), and 0.1% by weight for methanol. Thus,there was a difference in solubility among the solvents.

Comparative Example B2

[0177] It was confirmed that, upon a reaction of compound 2 prepared inComparative Example B1 with di-tert-amyl dicarbonate in THF in thepresence of 4-dimethylaminopyridine, compound 2 was converted tocompound 1.

What is claimed is:
 1. A process for producing a coloring material,comprising the steps of: providing a solution comprising (1) a solublepigment precursor which is convertible into an insoluble pigment, (2) asolvent capable of dissolving the soluble pigment precursor therein, and(3) a stabilizing agent comprising an organic compound having astructure or a functional group capable of stabilizing thedispersibility of the insolubilized pigment in the solvent; andconverting said soluble pigment precursor into an insoluble pigment toobtain the coloring material containing the insolubilized pigmentdispersed stably in the solvent.
 2. The process according to claim 1,further comprising the step of concentrating the resultant coloringmaterial to obtain a solidified coloring material.
 3. The processaccording to claim 2, further comprising the step of dispersing theresultant solidified coloring material in a solvent.
 4. The processaccording to claim 1, wherein the conversion of the soluble pigmentprecursor into the insoluble pigment is carried out by a chemicalmethod, a thermal method, a photolytic method, or a radiation inducedmethod or a combination thereof.
 5. The process according to claim 1,wherein the insoluble pigment has a polar group selected from the groupconsisting of a primary amine, a secondary amine, a cyclic amine, and ahydroxy group.
 6. The process according to claim 1, wherein thestabilizing agent has a group selected from the group consisting of >CO,—NH₂, >NH, >N—, ═N⁺<, —CONH₂, —CONH—, —NHCOO—, >NCOO—, —NHCONH—,(—NHCO)₂N—, and —OH.
 7. The process according to claim 1, wherein thestabilizing agent has an amine value.
 8. The process according to claim1, wherein the stabilizing agent has an amine value and an acid value,the amine value being greater than the acid value.
 9. The processaccording to claim 1, wherein the stabilizing agent has an amine valueof from 1 to 230 mg-KOH/g.
 10. The process according to claim 1, whereinthe stabilizing agent has a urethane bond.
 11. The process according toclaim 1, wherein the stabilizing agent has a molecular weight of notmore than 20,000.
 12. The process according to claim 1, wherein thestabilizing agent has 0.1 to 20 reactive double bond groups per moleculeon average.
 13. A coloring material produced by the process according toany one of claims 1, 2, and 3, for use in a color filter.
 14. A coloringmaterial comprising an adduct formed by interaction between (1) aninsoluble pigment produced by conversion from a soluble pigmentprecursor and (2) a stabilizing agent comprising an organic compoundhaving a structure or a functional group capable of stabilizing thedispersibility of the insolubilized pigment in a solvent.
 15. Thecoloring material according to claim 14, wherein the adduct is dispersedin the solvent.
 16. The coloring material according to claim 14, whereinthe insoluble pigment has a polar group selected from the groupconsisting of a primary amine, a secondary amine, a cyclic amine, and ahydroxy group.
 17. The coloring material according to claim 14, whereinthe stabilizing agent has a group selected from the group consistingof >CO, —NH₂, >NH, >N—, ═N⁺<, —CONH₂, —CONH—, —NHCOO—, >NCOO—, —NHCONH—,(—NHCO)₂N—, and —OH.
 18. The coloring material according to claim 14,wherein the stabilizing agent has an amine value.
 19. The coloringmaterial according to claim 14, wherein the stabilizing agent has anamine value and an acid value, the amine value being greater than theacid value.
 20. The coloring material according to claim 14, wherein thestabilizing agent has an amine value of from 1 to 230 mg-KOH/g.
 21. Thecoloring material according to claim 14, wherein the stabilizing agenthas a urethane bond.
 22. The coloring material according to claim 14,wherein the stabilizing agent has a molecular weight of not more than20,000.
 23. The coloring material according to claim 14, wherein thestabilizing agent has 0.1 to 20 reactive double bond groups per moleculeon average.
 24. The coloring material produced by the process accordingto claim 14, for use in a color filter.
 25. A color filter comprising acolored layer as colored pixels provided on a transparent substrate,said colored layer containing a coloring material, said coloringmaterial being produced by providing a solution comprising (1) a solublepigment precursor which is convertible into an insoluble pigment, (2) asolvent capable of dissolving the soluble pigment precursor therein, and(3) a stabilizing agent comprising an organic compound having astructure or a functional group capable of stabilizing thedispersibility of the insolubilized pigment in the solvent, andconverting said soluble pigment precursor into an insoluble pigment. 26.The color filter according to claim 25, wherein said colored layercomprises a light transparent resin with the insoluble pigment producedfrom the coloring material being dispersed therein.
 27. The color filteraccording to claim 26, wherein said transparent resin is anegative-working resist or positive-working resist or a polymer or aprepolymer which can be structured by crosslinking, polymerization, ordepolymerization induced by applying an ionizing radiation.
 28. Thecolor filter according to claim 25, wherein the coloring material is asolidified coloring material produced by, after the conversion of thesoluble pigment precursor in the solution to the insoluble pigment,concentrating the resultant coloring material to solidify the coloringmaterial.
 29. The color filter according to claim 28, wherein saidcolored layer is formed of a coating produced from the solidifiedcoloring material dispersed in a solvent.
 30. The color filter accordingto claim 25, wherein, in the coloring material, the conversion of thesoluble pigment precursor into the insoluble pigment is carried out by achemical method, a thermal method, a photolytic method, or a radiationinduced method or a combination thereof.
 31. The color filter accordingto claim 25, wherein, in the coloring material, the insoluble pigmenthas a polar group selected from the group consisting of a primary amine,a secondary amine, a cyclic amine, and a hydroxy group.
 32. The colorfilter according to claim 25, wherein, in the coloring material, thestabilizing agent has a group selected from the group consisting of >CO,—NH₂, >NH, >N—, ═N³⁰<, —CONH₂, —CONH—, —NHCOO—, >NCOO—, —NHCONH—,(—NHCO)₂N—, and —OH.
 33. The color filter according to claim 25,wherein, in the coloring material, the stabilizing agent has an aminevalue.
 34. The color filter according to claim 25, wherein, in thecoloring material, the stabilizing agent has an amine value and an acidvalue, the amine value being greater than the acid value.
 35. The colorfilter according to claim 25, wherein, in the coloring material, thestabilizing agent has an amine value of from 1 to 230 mg-KOH/g.
 36. Thecolor filter according to claim 25, wherein, in the coloring material,the stabilizing agent has an urethane bond.
 37. The color filteraccording to claim 25, wherein, in the coloring material, thestabilizing agent has a molecular weight of not more than 20,000. 38.The color filter according to claim 25, wherein, in the coloringmaterial, the stabilizing agent has 0.1 to 20 reactive double bondgroups per molecule on average.
 39. A color filter comprising a coloredlayer as colored pixels provided on a transparent substrate, saidcolored layer containing a coloring material, said coloring materialcomprising an adduct formed by interaction between (1) an insolublepigment produced by conversion from a soluble pigment precursor and (2)a stabilizing agent comprising an organic compound having a structure ora functional group capable of stabilizing the dispersibility of theinsolubilized pigment in a solvent.
 40. The color filter according toclaim 39, wherein said colored layer comprises a light transparent resinwith the insoluble pigment produced from the coloring material beingdispersed therein.
 41. The color filter according to claim 39, whereinsaid transparent resin is a negative-working resist or positive-workingresist or a polymer or a prepolymer which can be structured bycrosslinking, polymerization, or depolymerization induced by applying anionizing radiation.
 42. The color filter according to claim 39, wherein,in the coloring material, the adduct is dispersed in the solvent. 43.The color filter according to claim 39, wherein, in the coloringmaterial, the insoluble pigment has a polar group selected from thegroup consisting of a primary amine, a secondary amine, a cyclic amine,and a hydroxy group.
 44. The color filter according to claim 39,wherein, in the coloring material, the stabilizing agent has a groupselected from the group consisting of >CO, —NH₂, >NH, >N—, ═N⁺<, —CONH₂,—CONH—, —NHCOO—, >NCOO—, —NHCONH—, (—NHCO)₂N—, and —OH.
 45. The colorfilter according to claim 39, wherein, in the coloring material, thestabilizing agent has an amine value.
 46. The color filter according toclaim 39, wherein, in the coloring material, the stabilizing agent hasan amine value and an acid value, the amine value being greater than theacid value.
 47. The color filter according to claim 39, wherein, in thecoloring material, the stabilizing agent has an amine value of from 1 to230 mg-KOH/g.
 48. The color filter according to claim 39, wherein, inthe coloring material, the stabilizing agent has an urethane bond. 49.The color filter according to claim 25 or 39, wherein the insolublepigment contained in the colored pixel of the color filter has anaverage particle diameter in the range of from 1 to 300 nm and aparticle diameter distribution such that diameters of particlesconstituting the insoluble pigment are within ±30% of the averageparticle diameter and not more than 5% by weight of all the particlesare accounted for by particles having a diameter of not less than 300nm.
 50. The color filter according to claim 25 or 39, wherein thecontent of the insoluble pigment in the colored pixel of the colorfilter is in the range of from 10 to 90% by weight on a solid basis. 51.The color filter according to claim 25 or 39, wherein the colored pixelof the color filter has a contrast of not less than 2,000.
 52. The colorfilter according to claim 25 or 39, wherein, in a spectralcharacteristic curve in a visible region of the colored pixel of thecolor filter, the light transmittance in its light absorption region isin the range of from 0 to 20% while the light transmittance in its lighttransmission region is in the range of from 50 to 100%.
 53. A colorfilter comprising a colored layer as colored pixels provided on atransparent substrate, said colored layer containing apyrrolo[3,4-c]pyrrole derivative produced by converting at least oneketopyrrole group in a pyrrolo[3,4-c]pyrrole of formula

wherein A and B are each independently of the other a group of formula

wherein R₁ and R₂ are each independently of the other hydrogen, halogen,C₁-C₁₈ alkyl, C₂-C₁₈ alkoxy, C₁-C₁₈ alkylmercapto, C₁-C₁₈ alkylamino,—CN, —NO₂, phenyl, trifluoromethyl, C₅-C₆ cycloalkyl, —C═N-(C₁-C₁₈alkyl), a group of formula

imidazolyl, pyrrazolyl, triazolyl, piperazinyl, pyrrolyl, oxazolyl,benzoxazolyl, benzothiazolyl, benzimidazolyl, morpholinyl, piperidinyl,or pyrrolidinyl; G is —CH₂—, —CH(CH₃)—, —CH(CH₃)₂—, —CH═N—, —N═N—, —O—,—S—, —SO—, —SO₂— or —NR₇—; R₃ and R₄ are each independently of the otherhydrogen, halogen, C₁-C₁₈ alkoxy, or —CN; R₅ and R₆ are eachindependently of the other hydrogen, halogen, or C₁-C₆ alkyl; and R₇ ishydrogen or C₁-C₆ alkyl; and D and E are each independently of the othera group of formula

wherein, in the formulae (II), (III), and (IV), m, n, and p are eachindependently of one another a number of 0 or 1; X is C₁-C₁₄ alkylene orC₂-C₆ alkenylene; Y is a group -V-(CH₂)_(q)—; Z is a group-V-(CH₂)_(r)—; V is C₃-C₆ cycloalkylene; q is an integer from 1 to 6; ris an integer from 0 to 6; R and R are each independently of the otherhydrogen, C₁-C₆ alkyl, C₁-C₄ alkoxy, halogen, CN, NO₂, unsubstitutedphenyl or phenoxy, or phenyl or phenoxy which is substituted by C₁-C₄alkyl, C₁-C₄ alkoxy, or halogen; and Q is hydrogen, CN, Si(R₈)₃, a groupC(R₁₂)(R₁₃)(R₁₄) wherein R₁₂, R₁₃, and R₁₄ are halogen, a group offormula

wherein R₈ and R₉ are as defined above, a group SO₂R₁₅ or SR₁₅ whereinR₁₅ represents phenyl which is substituted by a C₁-C₄ alkyl, a C₁-C₄alkoxy, or a halogen, or a group of formula

R₁₀ and R₁₁ are each independently of the other hydrogen, C₁-C₁₈ alkyl,or a group of formula

wherein X, Y, R₈, R₉, m, and n are as defined above, or R₁₀ and R₁₁,together with the linking nitrogen atom, form pyrrolidinyl, piperidinyl,or morpholinyl radical; and D may be hydrogen, with the proviso that, ifD and/or E are a group of formula (III), Q is hydrogen, and n is 0, mmust be 1 and X must be a C₂-C₁₄ alkylene or C₂-C₈ alkenylene groupwhich is branched at the carbon atom attached to the oxygen atom, saidat least one ketopyrrole group being converted to

wherein A may be B with the proviso that, if A is B, D is E; and R′ isC₁-C₅ alkyl.
 54. The color filter according to claim 53, wherein A and Bin formula (V) are each independently of the other a group of formula

wherein R₁ and R₂ are each independently of the other hydrogen, chloro,bromo, C₁-C₄alkyl, C₁-C₆alkoxy, C₁-C₆ alkylamino, CN, or phenyl; G is—O—, —NR₇—, —N═N—, or —SO₂—; R₇ is hydrogen, methyl, or ethyl; and R₃and R₄ are hydrogen.
 55. The color filter according to claim 53, whereinA and B in formula (V) are identical to each other.
 56. The color filteraccording to claim 55, wherein A and B in formula (V) are a group offormula

wherein R₁ and R₂ are each independently of the other hydrogen, methyl,tert-butyl, chloro, bromo, CN, or phenyl.
 57. The color filter accordingto claim 53, wherein D is hydrogen or E, and E is a group of formula

or formula (IV) wherein, in formulae (VI), (VII), and (IV), m is 0 or 1;X is C₁-C₄ alkylene or C₁-C₅ alkenylene; R₈ and R₉ are eachindependently of the other hydrogen, C₁-C₄ alkyl, methoxy, chloro, or—NO₂—; Q is hydrogen, CN, CCl₃, a group of formula

wherein R₈ and R₉ are as defined above, SO₂, SH₃, or SCH₃; R₁₀ and R₁₁are each independently of the other hydrogen, C₁-C₄ alkyl, or a group offormula

or R₁₀ and R₁₁, taken together, form a piperidinyl radical, with theproviso that, if D and/or E are a group of formula (IX) and Q ishydrogen, X is a group of formula


58. The color filter according to claim 53, wherein D and E in formula(V) are identical to each other and are a group of formula


59. The color filter according to claim 53, wherein thepyrrolo[3,4-c]pyrrole derivative of formula (V) is produced by reactingthe pyrrolo[3,4-c]pyrrole of formula (I) in a solvent including a loweralcohol and in the presence of a base as a catalyst.
 60. The colorfilter according to claim 59, wherein the reaction is carried out at atemperature of 0 to 400° C., preferably a temperature of 20 to 200° C.,for 2 to 80 hr.
 61. The color filter according to claim 53, wherein thecoloring material containing the pyrrolo[3,4-c]pyrrole derivative offormula (V) according to claim 53 is contained in the colored layer. 62.The color filter according to claim 53, wherein the colored layercontains a coloring material containing as its component apyrrolo[3,4-c]pyrrole of formula

wherein A and B are as defined in formula (I), which has been producedin situ by thermal decomposition, photolysis, or chemical decompositionof the pyrrolo[3,4-c]pyrrole derivative according to claim
 53.

wherein R₁ and R₂ are each independently of the other hydrogen, halogen,C₁-C₁₈ alkyl, C₁-C₁₈ alkoxy, C₁-C₁₈ alkylmercapto, C₁-C₁₈ alkylamino,—CN, —NO₂, phenyl, trifluoromethyl, C₅-C₆ cycloalkyl, —C═N—(C₁-C₁₈alkyl), a group of formula

imidazolyl, pyrrazolyl, triazolyl, piperazinyl, pyrrolyl, oxazolyl,benzoxazolyl, benzothiazolyl, benzimidazolyl, morpholinyl, piperidinyl,or pyrrolidinyl; G is —CH₂—, —CH(CH₃)—, —CH(CH₃)₂—, —CH═N—, —N═N—, —O—,—S—, —SO—, —SO₂—, or —NR₇—; R₃ and R₄ are each independently of theother hydrogen, halogen, C₁-C₁₈ alkoxy, or —CN; R₅ and R₆ are eachindependently of the other hydrogen, halogen, or C₁-C₆ alkyl; and R₇ ishydrogen or C₁-C₆ alkyl; and D and E are each independently of the othera group of formula

wherein, in the formulae (II), (III), and (IV), m, n, and p are eachindependently of one another a number of 0 or 1; X is C₁-C₁₄ alkylene orC₂-C₆ alkenylene; Y is a group -V-(CH₂)_(q)—; Z is a group-V-(CH₂)_(r)—; V is C₃-C₆ cycloalkylene; q is an integer from 1 to 6; ris an integer from 0 to 6; R₈ and R₉ are each independently of the otherhydrogen, C₁-C₆ alkyl, C₁-C₄ alkoxy, halogen, CN, NO₂, unsubstitutedphenyl or phenoxy, or phenyl or phenoxy which is substituted by C₁-C₄alkyl, C₁-C₄ alkoxy, or halogen; and Q is hydrogen, CN, Si(R₈)₃, a groupC(R₁₂)(R₁₃)(R₁₄) wherein R₁₂, R₁₃, and R₁₄ are halogen, a group offormula

wherein R₈ and R₉ are as defined above, a group SO₂R₁₅ or SR₁₅ whereinR₁₅ represents phenyl which is substituted by a C₁-C₄ alkyl, a C₁-C₄alkoxy, or a halogen, or a group of formula

R₁₀ and R₁₁ are each independently of the other hydrogen, C₁-C₁₀ alkyl,or a group of formula

wherein X, Y, R₈, R₉, m, and n are as defined above, or R₁₀ and R₁₁,together with the linking nitrogen atom, form pyrrolidinyl, piperidinyl,or morpholinyl radical; and D may be hydrogen, with the proviso that, ifD and/or E are a group of formula (III), Q is hydrogen, and n is 0, mmust be 1 and X must be a C₂-C₁₄ alkylene or C₂-C₈ alkenylene groupwhich is branched at the carbon atom attached to the oxygen atom, saidat least one ketopyrrole group being converted to

wherein A may be B with the proviso that, if A is B, D is E; and R′ isC₁-C₅ alkyl.
 54. (Original) The color filter according to claim 53,wherein A and B in formula (V) are each independently of the other agroup of formula

wherein R₁ and R₂ are each independently of the other hydrogen, chloro,bromo, C₁-C₄ alkyl, C₁-C₆ alkoxy, C₁-C₆ alkylamino, CN, or phenyl; G is—O—, —NR₇—, —N═N—, or —SO₂—; R₇ is hydrogen, methyl, or ethyl; and R₃and R₄ are hydrogen.
 55. (Original) The color filter according to claim53, wherein A and B in formula (V) are identical to each other.

wherein R₁ and R₂ are each independently of the other hydrogen, methyl,tert-butyl, chloro, bromo, CN, or phenyl.
 57. (Original) The colorfilter according to claim 53, wherein D is hydrogen or E, and E is agroup of formula

or formula (IV) wherein, in formulae (VI), (VII), and (IV), m is 0 or 1;X is C₁-C₄ alkylene or C₁-C₅ alkenylene; R₈ and R₉ are eachindependently of the other hydrogen, C₁-C₄ alkyl, methoxy, chloro, or—NO₂—; Q is hydrogen, CN, CCl₃, a group of formula

wherein R₈ and R₉ are as defined above, SO₂, SH₃, or SCH₃; R₁₀ and R₁₁are each independently of the other hydrogen, C₁-C₄ alkyl, or a group offormula

or R₁₀ and R₁₁, taken together, form a piperidinyl radical, with theproviso that, if D and/or E are a group of formula (IX) and Q ishydrogen, X is a group of formula


58. (Original) The color filter according to claim 53, wherein D and Ein formula (V) are identical to each other and are a group of formula


59. (Original) The color filter according to claim 53, wherein thepyrrolo[3,4-c]pyrrole derivative of formula (V) is produced by reactingthe pyrrolo[3,4-c]pyrrole of formula (I) in a solvent including a loweralcohol and in the presence of a base as a catalyst.
 60. (Original) Thecolor filter according to claim 59, wherein the reaction is carried outat a temperature of 0 to 400° C., preferably a temperature of 20 to 200°C., for 2 to 80 hr.
 61. (Original) The color filter according to claim53, wherein the coloring material containing the pyrrolo[3,4-c]pyrrolederivative of formula (V) according to claim 53 is contained in thecolored layer.
 62. (Original) The color filter according to claim 53,wherein the colored layer contains a coloring material containing as itscomponent a pyrrolo[3,4-c]pyrrole of formula

wherein A and B are as defined in formula (I), which has been producedin situ by thermal decomposition, photolysis, or chemical decompositionof the pyrrolo[3,4-c]pyrrole derivative according to claim 53.